CN101802022B - 能量固化的光引发剂 - Google Patents
能量固化的光引发剂 Download PDFInfo
- Publication number
- CN101802022B CN101802022B CN200880107635.4A CN200880107635A CN101802022B CN 101802022 B CN101802022 B CN 101802022B CN 200880107635 A CN200880107635 A CN 200880107635A CN 101802022 B CN101802022 B CN 101802022B
- Authority
- CN
- China
- Prior art keywords
- thioxanthone
- phenyl
- photopolymerisable
- formula
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000000178 monomer Substances 0.000 claims abstract description 15
- 238000000576 coating method Methods 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 30
- -1 1-ethoxy Chemical group 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 230000001235 sensitizing effect Effects 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- VKQJCUYEEABXNK-UHFFFAOYSA-N 1-chloro-4-propoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OCCC)=CC=C2Cl VKQJCUYEEABXNK-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- ZSSOUAIRYPTMIN-UHFFFAOYSA-N 1-aminothioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N ZSSOUAIRYPTMIN-UHFFFAOYSA-N 0.000 claims description 2
- LCHAFMWSFCONOO-UHFFFAOYSA-N 2,4-dimethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3SC2=C1 LCHAFMWSFCONOO-UHFFFAOYSA-N 0.000 claims description 2
- JSLWEMZSKIWXQB-UHFFFAOYSA-N 2-dodecylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CCCCCCCCCCCC)=CC=C3SC2=C1 JSLWEMZSKIWXQB-UHFFFAOYSA-N 0.000 claims description 2
- OJIHXJHESAUYPR-UHFFFAOYSA-N 2-methoxyethyl 9-oxothioxanthene-3-carboxylate Chemical compound C1=CC=C2C(=O)C3=CC=C(C(=O)OCCOC)C=C3SC2=C1 OJIHXJHESAUYPR-UHFFFAOYSA-N 0.000 claims description 2
- WIYGQQIISXRPOW-UHFFFAOYSA-N butyl 7-methyl-9-oxothioxanthene-3-carboxylate Chemical compound C1=C(C)C=C2C(=O)C3=CC=C(C(=O)OCCCC)C=C3SC2=C1 WIYGQQIISXRPOW-UHFFFAOYSA-N 0.000 claims description 2
- ANJPBYDLSIMKNF-UHFFFAOYSA-N butyl 9-oxothioxanthene-4-carboxylate Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(C(=O)OCCCC)=CC=C2 ANJPBYDLSIMKNF-UHFFFAOYSA-N 0.000 claims description 2
- VYVRIXWNTVOIRD-LRHBOZQDSA-N ciguatoxin CTX1B Chemical compound C([C@@]12[C@@H](C)[C@@H]([C@@H]3[C@H]([C@H]([C@H](C)[C@H]4O[C@H]5C[C@@H](C)C[C@H]6O[C@@]7(C)[C@H](O)C[C@H]8O[C@H]9C=C[C@H]%10O[C@H]%11C[C@@H]%12[C@H]([C@@H]([C@H]%13O[C@H](C=CC[C@@H]%13O%12)\C=C\[C@H](O)CO)O)O[C@@H]%11C=C[C@@H]%10O[C@@H]9C\C=C/C[C@@H]8O[C@@H]7C[C@@H]6O[C@@H]5C[C@@H]4O3)O)O2)C)[C@H](O)CO1 VYVRIXWNTVOIRD-LRHBOZQDSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- GMZGPOQKBSMQOG-UHFFFAOYSA-N ethyl 3-(benzenesulfonyl)-9-oxothioxanthene-1-carboxylate Chemical compound C=1C=2SC3=CC=CC=C3C(=O)C=2C(C(=O)OCC)=CC=1S(=O)(=O)C1=CC=CC=C1 GMZGPOQKBSMQOG-UHFFFAOYSA-N 0.000 claims description 2
- PKUZBJXWIOTQFQ-UHFFFAOYSA-N ethyl 9-oxothioxanthene-2-carboxylate Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)OCC)=CC=C3SC2=C1 PKUZBJXWIOTQFQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- MLCOFATYVJHBED-UHFFFAOYSA-N methyl 9-oxothioxanthene-1-carboxylate Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)OC MLCOFATYVJHBED-UHFFFAOYSA-N 0.000 claims description 2
- 230000002794 monomerizing effect Effects 0.000 claims 1
- 238000000206 photolithography Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 82
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 54
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 229910052938 sodium sulfate Inorganic materials 0.000 description 20
- 235000011152 sodium sulphate Nutrition 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000013067 intermediate product Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 238000005406 washing Methods 0.000 description 10
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- RGZRSLKIOCHTSI-UHFFFAOYSA-N hydron;n-methylhydroxylamine;chloride Chemical compound Cl.CNO RGZRSLKIOCHTSI-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 230000002269 spontaneous effect Effects 0.000 description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 150000002790 naphthalenes Chemical class 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
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- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 2
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- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
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- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
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- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Indole Compounds (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT000073A ITVA20070073A1 (it) | 2007-09-17 | 2007-09-17 | Fotoiniziatori per reticolazione indotta dalla luce |
ITVA2007A000073 | 2007-09-17 | ||
PCT/EP2008/061726 WO2009037130A1 (en) | 2007-09-17 | 2008-09-05 | Photoinitiators for energy curing |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101802022A CN101802022A (zh) | 2010-08-11 |
CN101802022B true CN101802022B (zh) | 2013-03-27 |
Family
ID=39951618
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200880107635.4A Expired - Fee Related CN101802022B (zh) | 2007-09-17 | 2008-09-05 | 能量固化的光引发剂 |
Country Status (12)
Country | Link |
---|---|
US (1) | US20100196826A1 (de) |
EP (1) | EP2190887B1 (de) |
JP (1) | JP2010539270A (de) |
KR (1) | KR20100081316A (de) |
CN (1) | CN101802022B (de) |
AT (1) | ATE508143T1 (de) |
CA (1) | CA2699740A1 (de) |
DE (1) | DE602008006744D1 (de) |
DK (1) | DK2190887T3 (de) |
ES (1) | ES2365584T3 (de) |
IT (1) | ITVA20070073A1 (de) |
WO (1) | WO2009037130A1 (de) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2694688A1 (de) * | 2011-06-09 | 2014-02-12 | ANGUS Chemical Company | Zusammensetzung und verfahren zum entfernen von überschüssigem formaldehyd |
CN111574351A (zh) * | 2020-05-12 | 2020-08-25 | 北京化工大学常州先进材料研究院 | 一种长波长羟基甲基苯基酮类光引发剂及其制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1649905A (zh) * | 2002-04-26 | 2005-08-03 | 西巴特殊化学品控股有限公司 | 可引入的光敏引发剂 |
EP1617288A1 (de) * | 2004-07-15 | 2006-01-18 | Fuji Photo Film Co., Ltd. | Lichtempfindliche Zusammensetzung und Flachdruckplattenvorläufer |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3301885A (en) * | 1964-04-13 | 1967-01-31 | Velsicol Chemical Corp | Phenyl nu-hydrocarboxy nu-hydrocarbyl thiocarbamates |
JP2006316177A (ja) * | 2005-05-13 | 2006-11-24 | Toyo Ink Mfg Co Ltd | 重合性組成物、および重合物の製造方法 |
-
2007
- 2007-09-17 IT IT000073A patent/ITVA20070073A1/it unknown
-
2008
- 2008-09-05 DK DK08803696.7T patent/DK2190887T3/da active
- 2008-09-05 AT AT08803696T patent/ATE508143T1/de not_active IP Right Cessation
- 2008-09-05 WO PCT/EP2008/061726 patent/WO2009037130A1/en active Application Filing
- 2008-09-05 US US12/678,639 patent/US20100196826A1/en not_active Abandoned
- 2008-09-05 KR KR1020107007928A patent/KR20100081316A/ko not_active Application Discontinuation
- 2008-09-05 EP EP08803696A patent/EP2190887B1/de not_active Not-in-force
- 2008-09-05 JP JP2010524466A patent/JP2010539270A/ja not_active Ceased
- 2008-09-05 DE DE602008006744T patent/DE602008006744D1/de active Active
- 2008-09-05 CN CN200880107635.4A patent/CN101802022B/zh not_active Expired - Fee Related
- 2008-09-05 ES ES08803696T patent/ES2365584T3/es active Active
- 2008-09-05 CA CA2699740A patent/CA2699740A1/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1649905A (zh) * | 2002-04-26 | 2005-08-03 | 西巴特殊化学品控股有限公司 | 可引入的光敏引发剂 |
EP1617288A1 (de) * | 2004-07-15 | 2006-01-18 | Fuji Photo Film Co., Ltd. | Lichtempfindliche Zusammensetzung und Flachdruckplattenvorläufer |
Non-Patent Citations (1)
Title |
---|
JP特开2006-316177A 2006.11.24 |
Also Published As
Publication number | Publication date |
---|---|
ITVA20070073A1 (it) | 2009-03-18 |
ES2365584T3 (es) | 2011-10-07 |
CN101802022A (zh) | 2010-08-11 |
WO2009037130A1 (en) | 2009-03-26 |
EP2190887B1 (de) | 2011-05-04 |
CA2699740A1 (en) | 2009-03-26 |
ATE508143T1 (de) | 2011-05-15 |
EP2190887A1 (de) | 2010-06-02 |
DE602008006744D1 (de) | 2011-06-16 |
KR20100081316A (ko) | 2010-07-14 |
JP2010539270A (ja) | 2010-12-16 |
DK2190887T3 (da) | 2011-08-29 |
US20100196826A1 (en) | 2010-08-05 |
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